3-phenylpropyl N,N'-di(propan-2-yl)carbamimidate | 543724-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-phenylpropyl N,N'-di(propan-2-yl)carbamimidate
• CAS: 543724-42-1
• 化学式: C₁₆H₂₆N₂O
• 分子量: 262.395
• InChiKey: NVQQANGZQXPHFY-UHFFFAOYSA-N

物化性质

• 沸点：
  417.1±24.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylpropyl N,N'-di(propan-2-yl)carbamimidate 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以77%的产率得到1-氯-3-苯基丙烷
  参考文献：
  名称：

  一种温和，无膦的方法，可通过相应的O-烷基异脲将醇类转化为卤化物（Cl，Br，I）

  摘要：

  描述了将伯醇和仲醇转化为相应的烷基氯化物，溴化物和碘化物的新方法。在氯化物和溴化物的情况下，该转化是高产率的，可耐受一系列官能团，并且不依赖于膦的使用。

  DOI：

  10.1016/j.tetlet.2003.09.024
• 作为产物：
  描述：

  3-苯丙醇 、 N,N'-二异丙基碳二亚胺 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以100%的产率得到3-phenylpropyl N,N'-di(propan-2-yl)carbamimidate
  参考文献：
  名称：

  Microwave-Assisted Ester Formation Using O-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration

  摘要：

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.

  DOI：

  10.1021/jo900476y

文献信息

• Microwave-Assisted Ester Formation Using <i>O</i>-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration
  作者：Alessandra Chighine、Stefano Crosignani、Marie-Claire Arnal、Mark Bradley、Bruno Linclau

  DOI：10.1021/jo900476y

  日期：2009.7.3

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.
• A Novel Synthesis of 2-Alkylthiobenzothiazoles and 2-Alkylthiobenzoxazoles
  作者：Yanfei Yu、Zhengning Li、Lan Jiang

  DOI：10.1080/10426507.2011.636229

  日期：2012.5

  3H-Benzothiazole-2-thione and 3H-benzoxazole-2-thione were selectively S-alkylated by use of O-alkylisoureas as the alkylating reagents. The reactions could be performed under mild reaction conditions in short reaction times, and high yields were obtained using O-primary-alkylisoureas, whereas low yields were obtained with sec- and tert-alkylisoureas.
• A mild, phosphine-free method for the conversion of alcohols into halides (Cl, Br, I) via the corresponding O-alkyl isoureas
  作者：Zhengning Li、Stefano Crosignani、Bruno Linclau

  DOI：10.1016/j.tetlet.2003.09.024

  日期：2003.10

  A novel procedure for the conversion of primary and secondary alcohols into the corresponding alkyl chlorides, bromides and iodides is described. The transformation is high-yielding in the case of chlorides and bromides, tolerates a range of functional groups, and does not rely on the use of phosphines.

  描述了将伯醇和仲醇转化为相应的烷基氯化物，溴化物和碘化物的新方法。在氯化物和溴化物的情况下，该转化是高产率的，可耐受一系列官能团，并且不依赖于膦的使用。